SYNTHESIS OF DEUTERIUM-LABELED SALICYLCARNOSINE

Abstract

The effect of temperature on the effectiveness of the introduction of deuterium into a new biologically active compound salicylcarnosine (SC) has been studied. Deuterium gas and heavy water were used as a source of deuterium. The synthesis of labeled SC by the solid-phase method at 190°C leads to the production of [D]SC with a yield of 53%, and a deuterium content of about 4.8 atoms per molecule. During isotope exchange with deuterated water, it was shown that after pretreatment of the catalyst at room temperature with deuterium gas, isotope exchange between SC protons and deuterated water occurs more efficiently. [D]SC is formed with a yield of 46% and contains about 7.3 deuterium atoms per molecule. During the preparative synthesis of labeled SC according to this technique at 190°C, the yield of [D]SC was 60–70%, with a deuterium content of about 6.2 atoms per molecule. A new technique for activating the inclusion of deuterium in peptides opens up additional opportunities for obtaining highly labelled drugs.